WO2012007254A1 - Procédé de préparation sans isocyanate du polycarbonate-uréthane ou du polyester-uréthane - Google Patents

Procédé de préparation sans isocyanate du polycarbonate-uréthane ou du polyester-uréthane Download PDF

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Publication number
WO2012007254A1
WO2012007254A1 PCT/EP2011/060300 EP2011060300W WO2012007254A1 WO 2012007254 A1 WO2012007254 A1 WO 2012007254A1 EP 2011060300 W EP2011060300 W EP 2011060300W WO 2012007254 A1 WO2012007254 A1 WO 2012007254A1
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WIPO (PCT)
Prior art keywords
urethane
poly
carbonate
ester
catalyst
Prior art date
Application number
PCT/EP2011/060300
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English (en)
Inventor
Sophie Guillaume
Marion Helou
Jean-François Carpentier
Martine Slawinski
Original Assignee
Total Petrochemicals Research Feluy
Centre National De La Recherche Scientifique (Cnrs)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Total Petrochemicals Research Feluy, Centre National De La Recherche Scientifique (Cnrs) filed Critical Total Petrochemicals Research Feluy
Priority to EP11727684.0A priority Critical patent/EP2552993B1/fr
Priority to KR1020137000898A priority patent/KR101421389B1/ko
Priority to EA201270828A priority patent/EA022577B1/ru
Priority to JP2013519012A priority patent/JP5589140B2/ja
Priority to BR112013000857-1A priority patent/BR112013000857B1/pt
Priority to ES11727684.0T priority patent/ES2513568T3/es
Priority to US13/809,907 priority patent/US9080016B2/en
Priority to CN201180034823.0A priority patent/CN103003329B/zh
Publication of WO2012007254A1 publication Critical patent/WO2012007254A1/fr
Priority to US14/729,499 priority patent/US9365675B2/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
    • C08G63/08—Lactones or lactides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/64—Polyesters containing both carboxylic ester groups and carbonate groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C08G64/0216—Aliphatic polycarbonates saturated containing a chain-terminating or -crosslinking agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/02—Aliphatic polycarbonates
    • C08G64/0208—Aliphatic polycarbonates saturated
    • C08G64/0225—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen
    • C08G64/0241—Aliphatic polycarbonates saturated containing atoms other than carbon, hydrogen or oxygen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/30—General preparatory processes using carbonates
    • C08G64/305—General preparatory processes using carbonates and alcohols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/04—Polyurethanes

Definitions

  • the present invention discloses a method for preparing poly(carbonate-urethane) or poly(ester-urethane) without isocyanate.
  • Polyurethanes are widely used as paints, coatings, foams, adhesives, packaging in numerous fields such as automotive and consumer or domestic goods industries and in construction engineering or medicine as disclosed for example in Krol (P. Krol, Prog. Mater. Sci., 2007, 52, 915-1015), or in Szycher (M. Szycher, Szycher Handbook of polyurethanes; CRC press: Boca Raton, FL, 1999) or in Matsumura et al. (S. Matsumura, Y. Soeda, K. Toshima App!. Microbiol. Biotechnoi, 2006, 70, 12-20) or in Jayakumar et al. (R. Jayakumar, S. Nanjundan, M. Prabaharan, React.
  • PUs are generally prepared by polyaddition of diisocyanates and bi- or multifunctional polyols or hydroxyl terminal groups. PUs are thus multiblock copolymers of type (A-B) n , including alternating hard and soft sequences.
  • the soft flexible segments most commonly arise from polyether, polyester or polycarbonate diols.
  • the hard rigid segments most often consist of short-chain diisocyanates that impart physical crosslinking through hydrogen bonding thereby leading to higher melting temperature Tm than aliphatic polyesters or polycarbonates.
  • the macrodiols are biocompatible and biodegradable and presently easily derived from biomass.
  • PCUs Poly(carbonate-urethane)s (PCUs) without pendant hydroxyl groups have recently received some attention, although much less than poly(ester-urethane) and poly(ether-urethane).
  • PCUs are generally derived from soft carbonate segments of very low molar mass reacted with diisocyanates.
  • Soeda et al. (Y. Soeda, K. Toshima, S. Matsumara Macromol. Biosci., 2004, 4, 721 - 728) have reported a synthesis of PCU without such NCO-reactant. This involved first the formation of a diurethanediol having a molar mass of 320 g/mol through ring- opening of TMC with hexamethylenediamine, followed by its polycondensation reaction with diethyl carbonate using a lipase along with anisole and molecular sieves.
  • both soft segments and hard units remained very short, and shorter than the length obtained when using the diisocyanate route that is typically of 1 000 g/mol up to less than 12 000 g/mol.
  • the reaction conditions required heating over three days at a temperature of 1 10 °C.
  • the process afforded a mixture of PTMCUs having a number average molecular weight Mn of less than 20 000 g/mol and having three types of chain ends as identified by MALDI- ToF-MS. The yield was of 90% after purification. Modulating the soft block length remains however in need of optimisation,
  • Figure 1 represents typical 1 H NMR spectra for PTMC-(OH) 2 , PTMC-(COOH) 2 , and PTMC-(CH 2 DMC) 2 (300 MHz, CDCI 3 , 20 °C)
  • Figure 2 represents a typical Fourier Transformed InfraRed (ATR-FTIR, Shimadzu apparatus) spectrum of a PTMCHU expressed as %Transmittance versus cm "1 .
  • Figure 3 represents a typical 1 H NMR spectrum of a PTMCHU.
  • Figure 4 represents a typical Differential Scanning Calorimetry analysis of a PTMCHU (Setaram apparatus, 10 °C/min heating rate). It represents the heat flow expressed in mW as a function of temperature expressed in °C.
  • the present invention discloses a process for preparing poly(carbonate- urethane) (PCU) or poly(ester-urethane) (PEU) that comprises the steps of : a) immortal ring-opening polymerisation of a first 5, 6, 7-membered cyclic carbonate or cyclic ester, bearing or not functional groups, in the presence of a first catalyst system and one or more diols or polyols acting as co-initiators and chain transfer agents;
  • step c) polyaddition of a diamine or a polyamine via ring-opening of the second terminal 5, 6, or 7-membered cyclic carbonate of step c);
  • This method is exemplified schematically in scheme 1 for cyclic carbonates using trimethylene carbonate (TMC) for building the soft polycarbonate blocks and glycerol carbonate (DMC-CH 2 OH) as the connecting reagent.
  • TMC trimethylene carbonate
  • DMC-CH 2 OH glycerol carbonate
  • iROP 'Immortal' ring-opening polymerisation
  • TMC trimethylcarbonate
  • ⁇ -butyrolactone or lactide lactide
  • Suitable candidates for the first catalyst system can be found for example in EP-A- 2,096,132 They can be selected from metallic complexes of formula MR n wherein M is a metal Group 1 , 2, 3 (including the lanthanide series, hereafter referred as Ln), 8, 12 or 13 of the periodic Table, wherein each R is selected independently from hydrogen, hydrocarbyl radical having from 1 to 12 carbon atoms, alkoxide group OR * wherein R * is linear or branched hydrocarbyl having from 1 to 12 carbon atoms, amido group NR ** 2 wherein R ** is of general formula YR # 3 wherein Y is Si or C and each R # is independently selected from hydrogen or hydrocarbyl having from 1 to 12 carbon atoms, borohydride group or halide, and wherein n is the valence of M.
  • M is Mg(ll), Ca(ll), Y(lll), Fe(ll), Fe(lll), Zn(ll), Al(lll), or Bi(lll)
  • each R is selected independently from an amido group such as
  • an alkoxide group OR' such as OiPr, OMe, OCH 2 Ph, or a borohydride group (BH 4 ).
  • BDI amido-zinc ⁇ -diiminate
  • LO LO
  • M(OSO 2 CF 3 ) n Al or Bi as disclosed in EP-A-2,151 ,465.
  • the preferred organocatalyst precursors are preferably selected from 4-dimethylaminopyridine (DMAP) or 1 ,5,7-triazobicyclo-[4,4,0]dec-5-ene (TBD) or fe/t-butylimino-1 ,3dimethylperhydro-1 ,3,2diazaphosphine (BEMP). More preferably, it is BEMP.
  • DMAP 4-dimethylaminopyridine
  • TBD 1,5,7-triazobicyclo-[4,4,0]dec-5-ene
  • BEMP fe/t-butylimino-1 ,3dimethylperhydro-1 ,3,2diazaphosphine
  • the diol or polyol is used in excess and acts as initiator and transfer agent. It can be selected from any polyol of general formula R(OH) n where n is equal to 2 or more and R is a linear or branched, aliphatic or aromatic hydrocarbyl having up to 20 carbon atoms, or any combination thereof. Most preferably, it is 1 ,3- and/or 1 ,2- propanediol and/or glycerol and/or pentaerythritol. These polyols can be derived from bioresources.
  • the carbonate or ester monomer-to-diol/polyol ratio can be varied in the range 10,000:1 to 10:1 ; preferentially, it is in the range 1 ,000:1 to 100:1 .
  • the monomer-to- catalyst ratio can be varied in the range 1 ,000,000:1 to 100:1 ; preferentially, it is from 500,000:1 to 10,000:1 .
  • the chemical modification of the hydroxyl chain end groups into carboxylic end groups of step b) is carried out in the presence of a second catalyst system. It is described for example in Yu and Zhuo (F. Yu, R. Zhuo, Polymer J. 2003, 8, 671 -676) or in Lee et al. (S.-H. Lee, S. H. Kim, Y.-K. Han, Y. H. Kim J. Poiym. Sci. A Poiym. Chem, 2001 , 39, 973-985) or in Jeon et al. (O. Jeon, S.-H. Lee, S. H. Kim, Y. M. Lee, Y. H. Kim Macromolecules, 2003, 36, 5585-5592).
  • step a) It can be carried out by reacting the polycarbonate or polyester obtained in step a) with any suitable anhydride, optionally in an inert solvent selected for example from 2-methyltetrahydrofuran, furan, 1 ,4-dioxane, or any aliphatic or aromatic hydrocarbon.
  • the second catalyst system can be selected from any suitable catalyst traditionally used for opening of an anhydride with an alcohol.
  • it can be pyridine or a mixture of triethylamine and 4-dimethylaminopyridine (DMAP), loaded in amounts of 0.1 to 5% with respect to the polymer formed in step a)
  • the reaction is carried out at a temperature of from 0 to 80 °C, preferably from 15 to 50 °C and more preferably at room temperature for a period of time of 1 hour to 2 days, preferably from 2 to 24 hours.
  • the coupling reaction of step c) is carried out in the presence of a third catalyst system. It is carried out by reacting at least 2 equivalents of a second 5, 6, or 7- membered cyclic carbonate, bearing at least one functional group enabling coupling with the carboxylic moiety, optionally in the presence of a coupling agent such as dicyclohexylcarbodiimide (DCC) and a suitable catalyst such as for example pyridine or DMAP or N-hydroxybenzotriazole (HOBt) loaded in amounts of 0.1 to 5% with respect to the functional cyclic carbonate, optionally in an inert solvent selected for example from 2-methyltetrahydrofuran, furan, dichloromethane or any aliphatic or aromatic hydrocarbon.
  • DCC dicyclohexylcarbodiimide
  • HOBt N-hydroxybenzotriazole
  • the polyaddition reaction d) is carried out by adding to the compound obtained in step c) a diamine or a polyamine of general formula R(NH 2 ) n where n is equal to 2 or more and R is a linear or branched, aliphatic or aromatic hydrocarbyl having from 1 to 12 carbon atoms, or any combination derived thereof. Preferably, it can be 1 ,6- hexamethyienediamine.
  • the amine can contain a functional group which will provide pendant functions on the main chain. This functional group can be used for various purposes.
  • NH 2 /cycl c carbonate ratio can be varied from 0.5 to 5; more preferably it is from 0.8 to 1 .5. This ratio affects the molecular weight of the PCUs or PEUs eventually recovered.
  • the NH 2 /cyclic carbonate ratio is preferentially close to 1 .
  • the poiyaddition reaction d) can be optionally performed in an inert solvent selected for example from 2- methyltetrahydrofuran, furan, 1 ,4-dioxane, or any aliphatic or aromatic hydrocarbon.
  • the reaction is performed at a temperature ranging from 20 °C to 250 °C. Higher temperatures favour the formation of higher molecular weight products.
  • the present invention also covers poiy(carbonate-urethane) or poly(ester-urethane) obtained by the method described hereabove. They are characterised in that the polycarbonate soft segments are long and that the segments' length can be monitored by the ring-opening polymerisation conditions. The long soft
  • polycarbonate segments typically have molecular weights Mn ranging between 10,000 and 250,000 g/mol, preferably between 50,000 and 100,000 g/mol.
  • the bulk iROP of TMC (1 .10 g, 10.8 mmol) was carried out at a temperature of 60 °C using a catalytic system based on the amido zinc ⁇ -diiminate, ((BDI lPr )Zn(N(SiMe3)2 (7 mg, 0.0108 mmol) and 1 ,3-propanediol (15.8 ⁇ _, 0.218 mmol) as co-initiator and as chain transfer agent. It afforded 1 .05 g of ⁇ , ⁇ -dihydroxy telechelic PTMCs, PTMC-(OH) 2 as seen in Scheme 1 with a yield of 100%.
  • Figure 1 displays the 1 H NMR spectra of the dihydroxy precursor PTMC-(OH) 2 and the parent ⁇ , ⁇ -dicarboxylate telechelic PTMC-(COOH) 2 .
  • Such data evidenced the quantitative functionalisation of PTMC by the carboxylic units.
  • the polydispersity index values of PTMCs were respectively of 1 .32 for PTMC-(OH) 2 , 1 .24 for PTMC-(COOH) 2 , and 1 .31 for PTMC-(CH 2 DMC) 2 . These polydispersities remained narrow throughout the various manipulations, thus demonstrating the efficiency of the procedures to selectively react with the terminal functions without deteriorating the carbonate backbone chain.
  • Figure 3 represents a typical 1 H NMR spectrum of a PTMCHU
  • Figure 4 represents a typical Differential Scanning Calorimetry analysis of a PTMCHU (Setaram apparatus, 10 °C/min heating rate) PAGE INTENTIONALLY LEFT BLANK

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé permettant de préparer du polycarbonate-uréthane ou du polyester-uréthane sans isocyanate.
PCT/EP2011/060300 2010-07-15 2011-06-21 Procédé de préparation sans isocyanate du polycarbonate-uréthane ou du polyester-uréthane WO2012007254A1 (fr)

Priority Applications (9)

Application Number Priority Date Filing Date Title
EP11727684.0A EP2552993B1 (fr) 2010-07-15 2011-06-21 Procédé de préparation sans isocyanate du polycarbonate-uréthane ou du polyester-uréthane
KR1020137000898A KR101421389B1 (ko) 2010-07-15 2011-06-21 이소시아네이트-부재의, 폴리(카르보네이트-우레탄) 또는 폴리(에스테르-우레탄)의 제조 방법
EA201270828A EA022577B1 (ru) 2010-07-15 2011-06-21 Безизоцианатный способ получения поли(карбонат-уретана) или сложного поли(эфир-уретана)
JP2013519012A JP5589140B2 (ja) 2010-07-15 2011-06-21 ポリ（カーボネート−ウレタン）またはポリ（エステル−ウレタン）のイソシアネートフリーな製造方法
BR112013000857-1A BR112013000857B1 (pt) 2010-07-15 2011-06-21 método livre de isocianato para a preparação de poli (carbonato-uretano) ou poli (éster-uretano)
ES11727684.0T ES2513568T3 (es) 2010-07-15 2011-06-21 Procedimiento de preparación sin isocianato de poli(carbonato-uretano) o poli(éster-uretano)
US13/809,907 US9080016B2 (en) 2010-07-15 2011-06-21 Isocyanate-free method for preparing poly(carbonate-urethane) or poly(ester-urethane)
CN201180034823.0A CN103003329B (zh) 2010-07-15 2011-06-21 聚(碳酸酯-氨基甲酸酯)或聚(酯-氨基甲酸酯)的不使用异氰酸酯的制备方法
US14/729,499 US9365675B2 (en) 2010-07-15 2015-06-03 Isocyantate-free method for preparing poly(carbonate-urethane) or poly(ester-urethane)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP10290398 2010-07-15
EP10290398.6 2010-07-15

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US13/809,907 A-371-Of-International US9080016B2 (en) 2010-07-15 2011-06-21 Isocyanate-free method for preparing poly(carbonate-urethane) or poly(ester-urethane)
US14/729,499 Continuation US9365675B2 (en) 2010-07-15 2015-06-03 Isocyantate-free method for preparing poly(carbonate-urethane) or poly(ester-urethane)

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Publication Number Publication Date
WO2012007254A1 true WO2012007254A1 (fr) 2012-01-19

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PCT/EP2011/060300 WO2012007254A1 (fr) 2010-07-15 2011-06-21 Procédé de préparation sans isocyanate du polycarbonate-uréthane ou du polyester-uréthane

Country Status (9)

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US (2) US9080016B2 (fr)
EP (1) EP2552993B1 (fr)
JP (1) JP5589140B2 (fr)
KR (1) KR101421389B1 (fr)
CN (1) CN103003329B (fr)
BR (1) BR112013000857B1 (fr)
EA (1) EA022577B1 (fr)
ES (1) ES2513568T3 (fr)
WO (1) WO2012007254A1 (fr)

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WO2014068250A1 (fr) * 2012-11-05 2014-05-08 Bostik Sa Polymères à faible masse molaire comprenant au moins un groupement terminal 4-méthyléther-1,3-dioxolan-2-one
WO2014091173A1 (fr) * 2012-12-14 2014-06-19 Bostik Sa Polymères hydrocarbonés comportant deux groupements terminaux à terminaisons 2-oxo-1,3-dioxolan-4-yl, leur préparation et leur utilisation
US9062160B1 (en) 2014-01-23 2015-06-23 International Business Machines Corporation Catalyst-free methods of forming polyurethanes from pentafluorophenyl carbonates
US9062228B2 (en) 2011-12-30 2015-06-23 E I Du Pont De Nemours And Company Aqueous inkjet inks containing polyurethane binders with components to interact with cellulose
US9315690B2 (en) 2011-12-30 2016-04-19 E I Du Pont De Nemours And Company Aqueous pigment dispersions based on polyurethane dispersants having components to interact with cellulose
WO2016124518A1 (fr) 2015-02-05 2016-08-11 Evonik Degussa Gmbh Synthèse sans isocyanate de polymères modifiés par carbonate
EP2997072A4 (fr) * 2013-05-16 2017-01-11 Cyclicor AB Uréthanes, leurs polymères, compositions d'enduction et leur production à partir de carbonates cycliques
EP3401350A1 (fr) 2017-05-11 2018-11-14 Henkel AG & Co. KGaA Procédé de production de polyesters fonctionnalisés
EP3401348A1 (fr) 2017-05-11 2018-11-14 Henkel AG & Co. KGaA Procédé de production de polyesters fonctionnalisés
FR3073849A1 (fr) * 2017-11-22 2019-05-24 Bostik Sa Polyurethane a terminaisons (5-alkyl-1,3-dioxolen-2-one-4-yl)
FR3073847A1 (fr) * 2017-11-22 2019-05-24 Bostik Sa Polyurethane a terminaisons (5-alkyl-1,3-dioxolen-2-one-4-yl) et ses utilisations
EP3670618A1 (fr) 2018-12-20 2020-06-24 Henkel AG & Co. KGaA Procédé de production de polyesters fonctionnalisés

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US9000101B2 (en) * 2013-07-10 2015-04-07 Xerox Corporation Anhydride end-capping of polymers
CN104231191B (zh) * 2014-09-16 2018-04-24 上海金力泰化工股份有限公司 水性非异氰酸酯聚氨酯改性的聚酯的制备方法
BR112017028598B1 (pt) * 2015-06-30 2021-12-14 Evonik Operations Gmbh Composições de poliuretano livres de isocianato e uso das referidas composições
JP6341888B2 (ja) * 2015-07-02 2018-06-13 大日精化工業株式会社 ポリヒドロキシウレタン樹脂及びその製造方法
CN114031767A (zh) * 2021-12-07 2022-02-11 广东普赛达密封粘胶有限公司 一种环状碳酸酯预聚物、硅烷改性非异氰酸酯聚氨酯树脂及其制备方法和应用

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